4-Nitrobenzoic Acid → N-(3,5-dimethylphenyl)-4-nitrobenzamide

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:1][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=2)=[O:18])=[CH:20][CH:21]=1)([O-:12])=[O:11]

Participants

Reactant 2

HCID 61084-Nitrobenzoic Acid

HCID 79493,5-Dimethylaniline

Product 1

HCID 2843294N-(3,5-dimethylphenyl)-4-nitrobenzamide

Procedure

Using 3,5-xylidine (1.42 ml, 11.0 mmol) and 4-nitrobenzoic acid (1.76 g, 10.4 mmol), the procedure of Reference Example 16 was repeated to obtain 2.72 g (quantitative) of the title compound in the form of light yellow crystals.

Sources & evidence

ORD record: ord-faf03e3b2ef74ea6adbc16e6e6d66bc2
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728835

Reaction notes

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